Metal-free difunctionalization of alkynes leading to alkenyl dithiocyanates and alkenyl diselenocyanates at room temperature

A simple and practical method for the synthesis of alkenyl dithiocyanates and alkenyl diselenocyanates has been developed via stereoselective difunctionalization of alkynes with NaSCN or KSeCN at room temperature. Through this methodology, a series of alkenyl dithiocyanates and alkenyl diselenocyana...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 46; pp. 9064 - 9068
Main Authors Lu, Ling-Hui, Zhou, Si-Jia, He, Wei-Bao, Xia, Wen, Chen, Ping, Yu, Xianyong, Xu, Xinhua, He, Wei-Min
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.11.2018
Royal Society of Chemistry
Subjects
Alkynes
Chemistry
Chemistry, Organic
Oxidants
Oxidizing agents
Physical Sciences
Room temperature
Science & Technology
Sodium thiocyanate
Stereoselectivity
QUINOLINE N-OXIDES
AROMATIC KETONES
ONE-POT SYNTHESIS
BASE-FREE
C-3 THIOCYANATION
ALKYNYLCARBONYL COMPOUNDS
SELECTIVE SYNTHESIS
SPIROCYCLIZATION
TRIFLUOROMETHYL SULFIDES
C-H
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Summary:A simple and practical method for the synthesis of alkenyl dithiocyanates and alkenyl diselenocyanates has been developed via stereoselective difunctionalization of alkynes with NaSCN or KSeCN at room temperature. Through this methodology, a series of alkenyl dithiocyanates and alkenyl diselenocyanates could be efficiently and conveniently obtained in moderate to good yields under mild and metal-free conditions by the simple use of oxone and PhI(OAc) 2 as the oxidants.
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/C8OB02368A